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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:18:07 UTC
HMDB IDHMDB0006569
Secondary Accession Numbers
  • HMDB06569
Metabolite Identification
Common Name6'-Sialyllactose
DescriptionSialyllactose is an oligossaccharide found in both human breast milk and cow's milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin.
Structure
Thumb
Synonyms
ValueSource
(2>6')-a-sialyllactoseHMDB
(2>6')-alpha-sialyllactoseHMDB
(2>6')-sialyllactoseHMDB
6'-a-SialyllactoseHMDB
6'-alpha-SialyllactoseHMDB
6'-MonosialyllactoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucoseHMDB
(2R,4S,5R,6R)-4-Hydroxy-5-[(1-hydroxyethylidene)amino]-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
6'-SialyllactoseMeSH
Chemical FormulaC23H39NO19
Average Molecular Weight633.5511
Monoisotopic Molecular Weight633.211628071
IUPAC Name(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number35890-39-2
SMILES
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C23H39NO19/c1-7(28)24-13-8(29)2-23(22(38)39,43-20(13)15(34)10(31)4-26)40-6-12-16(35)17(36)18(37)21(41-12)42-19(11(32)5-27)14(33)9(30)3-25/h3,8-21,26-27,29-37H,2,4-6H2,1H3,(H,24,28)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20+,21-,23+/m0/s1
InChI KeyVMWYCXKMRSTDSP-GIGDJUIZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organopnictogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-Gal-(1->3)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:53481 )
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified151.5644221+/- 11.1809820 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected and Quantified119 +/- 54.9 uMAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021796
KNApSAcK IDNot Available
Chemspider ID559069
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643987
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePozsgay, Vince; Jennings, Harold J.; Kasper, Dennis L. A novel approach to N-acetylneuraminic acid-containing oligosaccharides. Synthesis of a glycosyl donor derivative of a-N-acetyl-D-neuraminyl-(2 ® 6)-D-galactose. Journal of Carbohydrate Chemistry (1987), 6(1), 41-55.
Material Safety Data Sheet (MSDS)Not Available
General References